Lloyd Blankfein, Goldman Sachs CEOReuters/ Lucas JacksonGoldman Sachs CEO Lloyd Blankfein rocks a Swatch with what appears to be a clear plastic band. Swatch's tend to range between $50 to $245. It's also not exactly the sort of timepiece you'd expect a chief executive of a Wall Street investment bank to wear. Then again, Goldman is "the most hipster" bank on Wall Street.

Jack Bogle, Founder of the Vanguard GroupReuters/ Tim ShafferInvesting legend Jack Bogle, the founder of the Vanguard Group, wears a $14 wristwatch he received from a shareholder.

"I received in the mail a wristwatch from a devoted shareholder in California. On the dial were printed our Vanguard logo, my name, and a phrase that was an indication I was still looking out for our shareholders: "Still on Watch." It was also an outrageous pun: "Still on Watch." Confident that it would be my rabbit’s foot, I put the watch on my wrist, where, having proved itself, it remains to this day. (Yes, I knew about the $50 limit on gifts. So I checked the catalog for the price. It was $14. Talk about value!)," he wrote.

Carl Icahn, Icahn EnterprisesTime MagazineBillionaire Carl Icahn, the famed activist investor, appears to wear The A Lange & Sohne Grosse Langematik Gangreserve in this TIME magazine cover from December 2013.

George Soros, Soros Fund ManagementReuters/ Bobby YipHedge fund legend George Soros was seen wearing this Patek Aquanaut back in 2010.

Bond guru Jeff Gundlach, CEO of DoubleLine CapitalReuters/ Jessica RinaldiWe learned about Jeff Gundlach's watch collection when he had a bunch of his artwork and personal property stolen in 2012. According to the Santa Monica Police Department report, the watches that were stolen included a Glashutte, Breitling, A. Lange & Sohne, TAG Heuer, and a Patek Philippe. We couldn't nail down prices for these specific models, but every one can run in the tens of thousands of dollars or more.